“This mystery surrounding Grant’s character has made it challenging for historians to explain his extraordinary turnaround from 1854—when he was forced out of the military—to 1864, when he was promoted to general-in-chief of the United States Army.”

By John Reeves

SHORTLY AFTER the death of Ulysses S. Grant on July 23, 1885, William Tecumseh Sherman told a former colleague that, “Grant’s whole character was a mystery even to himself—a combination of strength and weakness not paralleled by any of whom I have read in ancient or modern history.”

This mystery surrounding Grant’s character has made it challenging for historians to explain his extraordinary turnaround from 1854—when he was forced out of the military—to 1864, when he was promoted to general-in-chief of the United States Army.

Grant had obvious weaknesses as a potential military leader prior to the Civil War. He had struggled to make a living as a civilian from 1854 to 1861. And having been a quartermaster during the Mexican War, he had never commanded troops in battle.

When Grant first took over a regiment in 1861, he skimmed an old book on tactics, writing later, “I do not believe the officers of the regiment ever discovered that I never studied tactics that I used.” Nevertheless, Grant had three remarkable leadership attributes that emerged during the Civil War that help explain his success on the battlefield. In this article, we’ll take a closer look at each of them.

Grant had faith in the Union cause

On the morning of April 6, 1862, Grant’s army was surprised at Pittsburg Landing, Tennessee, which resulted in the bloody Battle of Shiloh.

Confederate forces under General Albert Sidney Johnston drove Union troops back toward the Tennessee River for most of the day. One Union staff officer succinctly summarized what happened.

“We were attacked by vastly superior numbers on Sunday and were crowded hard and forced gradually to contract our lines during the whole day.”

By 5 p.m. on that first day of the battle, everything looked hopeless for the Federals. The writer Ambrose Bierce—a Union soldier at the time—described the thousands of Northern stragglers by the riverbank.

“These men were deaf to duty and dead to shame,” he wrote.

Grant may have been the only person in the entire Union Army, who still believed in victory at that perilous time. In his memoirs, Grant wrote, “There was in fact, no hour during the day when I doubted the eventual defeat of the enemy.” Ultimately, Grant’s troops held on and were able to defeat the rebels on the second day of battle.

Sherman famously described going to Grant during the evening after the first day of carnage to suggest retreating. Losing his nerve at the last minute, Sherman merely said, “Well Grant, we’ve had the devil’s own day, haven’t we?” Grant replied simply, “Yes, lick ‘em tomorrow, though.”

Two years later, after Grant became general-in-chief, Sherman told him: “The chief characteristic in your nature is the simple faith in success you have always manifested, which I can liken nothing else than the faith a Christian has in a Savior. This faith gave you victory at Shiloh…”

The reason he possessed this simple faith is that Ulysses S. Grant always believed in the destiny of the United States as one country from the Atlantic Ocean to the Mississippi Valley to the Pacific Ocean.

Grant understood risk management and used it to his advantage

In late 1862 and early 1863, Grant had tried various schemes for seizing Vicksburg, Mississippi. All had ended in failure. Eventually, he settled on a bold new plan. He would send a flotilla of gunboats and transports past the Vicksburg batteries, while moving his troops down the west bank of the Mississippi River, where they would eventually be transported to a landing site across the water; they’d then move north, threatening both Vicksburg and Jackson, Mississippi. It seemed like a high-risk strategy.

“I tremble for the result,” Sherman told his wife. “I look upon the whole thing as one of the most hazardous and desperate moves of this or any other war.”

Despite Sherman’s concerns, Grant’s plan ultimately led to the surrender of Vicksburg. It was arguably Grant’s greatest victory. His huge gamble had paid off.

It may not have been that big of a gamble after all, however. Grant understood the principle of positive optionality and acted accordingly. Positive optionality allows you to manage risk on the downside, while taking advantage of a potentially huge upside.

Grant believed the riskiness of each step of his plan could be controlled, allowing him to benefit from any upside that emerged. The running of the batteries, for example, was a manageable risk. If the fleet was severely damaged by the action, then crossing the troops into Mississippi might be jeopardized or delayed. But Grant would still have his army.

Landing his army in Mississippi became another manageable risk, especially since he knew that his opposing commander was extremely risk averse and likely wouldn’t commit enough troops to stop him south of Vicksburg.

In a book about risk called Antifragile: Things That Gain from Disorder, Nassim Nicholas Taleb notes that “fragile” hates volatility, while “antifragile” benefits from volatility. During the Vicksburg Campaign, Grant appeared to be antifragile, while rebel forces seemed fragile.

Later in the war, when Grant was asked if he was really certain of a decision, he said, “No, I am not, but in war anything is better than indecision. We must decide. If I am wrong, we shall soon find it out, and can do the other thing. But not to decide wastes both time and money, and may ruin everything.”

To contemporaries, Grant may have looked like a gambler. In reality, he took smart risks when he knew he’d benefit from the chaos of the battlefield.

Grant was more persistent than other Union commanders

During the Battle of the Wilderness on May 5 and May 6, 1864, Grant’s performance was mixed. He had ended up fighting in an area he probably should’ve avoided. And on the second day of the fighting, he almost had his left turned at midday, and then later, nearly had his right turned. The North lost almost 18,000 men in this horrific bloodbath—Joseph Hooker retreated after similar losses a year earlier at the Battle of Chancellorsville.

But Grant had no intention of turning back and remained committed to his overall strategic plan. On May 7, 1864, Grant ordered his army to march southeast to Spotsylvania Court House that evening. It may have been the turning point of the war. Generals George McClellan, Ambrose Burnside, and Hooker had all turned back after violent Confederate resistance in previous campaigns. Grant continued moving forward. His persistence was one of his finest attributes. His aide Horace Porter later wrote: “The night march had become a triumphal procession for the new commander.”

The journalist Whitelaw Reid said of Grant, he was “terrible in a determination that was stopped by no question of cost; stolid as to slaughter or famine or fire, so they led to his goal.”

John Reeves is the author of Soldier of Destiny: Slavery, Secession, and the Redemption of Ulysses S. Grant. You can follow him on Twitter ‘X’ at @reevesjw.